HBO's Insecure: Can We Discuss Issa Rae's Style Evolution?

photo: courtesy hbo

Wait a sec, we really need to discuss Issa’s style evolution throughout the last three seasons of Insecure, because it was dramatic and amazing.

Hard to pin down, but it felt like Issa’s style could be described as Afrocentric and modern, but also art hipster and it really unfolded season after season as her confidence grew. Let’s dive into this evolution, starting with season one.

Season One:

In the first season, we met our awkward but hilarious heroine, Issa Dee. We followed her as she battled everyday life struggles like a five-year relationship with an unemployed boyfriend that came to a halt, passive aggressive coworkers who send secret emails behind her back, and her questionable decision making. As if all of that weren't enough, she turned twenty-nine and was far from the “Adult Issa” she pictured she would be (not an unfamiliar revelation for most).

photo: courtesy hbo

Issa looked great in patterns. Whether they were very tribal or a super loud print she always looked comfortable and owned it. It was natural for her to stand out in the bright colors a lot of other people would shy away (based on her style choices, I would peg her as a Pisces or Gemini Rising btw).

Issa knew where to find the blazers too! From the vintage and oversized, business cut, and even the canary yellow; her blazer game was on point. Also, in the first season we got to see what was the beginning of some really dope graphic tee appearances. My favorite for the season being the Prince cover art graphic.

photo: courtesy hbo

Issa’s hairstyles evolved too! Issa wore a beautiful-natural shortcut with auburn-brown coloring that suited her skin tone perfectly. And, she maintained throughout the season. By season three, she wore sleek, crossway cornrows that fed into one long, looped braid that she gracefully sat to one side. It was so simple and elegant and allowed you to see the structure of her face really well. But, we'll get to that later!

PHOTO: COURTESY HBO

PHOTO: COURTESY HBO

Season Two:

Season two brought a whole new level of Issa madness! Newly single and out in the dating world for the first time in how long? Also, she was living alone, had gone through some major career changes, and was trying to figure out how to keep her “hoe-tation” in check. Although, her life was a mess she brought some style confidence that I am sure all fans were eager to get into. “New Season, New Me”, right?

photo: courtesy hbo

The hair switch up! Throughout the whole season, she set the example for how versatile a short natural cut can be. She would sometimes make it exciting and fun with a high updo, or sleek and sexy pulled to the back. She even gave her afro a unique flair with small braids in the front.

Most styles were intricate with twists here or rubber bands there. It allowed the eyes to wonder and kept you visually stimulated. Her accessories this season were also a pleasant add-on to the visual wonderment. Issa gave us big hoops, dangling jewels, and tribal pieces.

We got to see more of those dope tees in season two as well! Now becoming an Issa staple, fans of hers really looked forward to what the latest graphic would showcase. The graphics she chose cooly made social commentary and noted to pop culture influences so it was always interesting to see what would be the latest statement.

PHOTO: COURTESY HBO

PHOTO: COURTESY HBO

PHOTO: COURTESY HBO

PHOTO: COURTESY HBO

Issa’s style choices in season two felt like we were beginning to see the evolution of her style power. Her confidence was building but how would that influence Issa’s style identity? Was her style 90s vintage hipster? Or was it more Afrocentric modernism? Was it both? For season three I was eager to see all of that Issa personality to come out in very unique style choices.

PHOTO: COURTESY HBO

Season Three:

Season three started with Issa couch-surfing and ended with what looks like the beginning of her living her best life! This season invited a new love interest, a career change, and blossoming new passion projects for our heroine. Aside from that, we watched fun times on a ferris wheel, Molly Squared, and some girlfriend group blowouts. What was most interesting though was seeing the ghost of boyfriends past. I guess they do always come back right when you stop thinking about them, huh?

PHOTO: COURTESY HBO

Style-wise, I felt this was the season that the real Issa Dee came through! Her hairstyles were intricate and her accessories and outfits were on point. What was unexpected was how flawless her makeup was throughout the entire season.

From eyebrows to lashes and liner, to the nude brown lip shade, it was all so well-done. It all came together to speak towards her growing confidence and the readiness to go after what she really wants in life.

She played with color and patterns to the extreme, her graphic tees were still coming in hot, and you finally got to see what makes Issa’s style so Issa. See what happens when you drop failing relationships and dead-end jobs?

PHOTO: COURTESY HBO

PHOTO: COURTESY HBO

Now, I’m about to reveal my top two favorite looks of last season.

The first favorite look was at Tiffany’s baby shower. I couldn't take my eyes off her the whole scene. She wore a beige, knit polo with a marigold striped, high waisted skirt. The two patterns coming together felt very modern but with a small hint of femininity because of the soft colors.

She accented gold in her necklace and earrings which coordinated well with the neutral colors in her clothes. Her hair was again intricately twisted up into a subtle mohawk. This was the perfect daytime event look and I will be figuring out where the pieces came from so I can copy.

PHOTO: COURTESY HBO

PHOTO: COURTESY HBO

The second favorite look was her birthday ensemble. It may just be the standard “do more” birthday effort but I really saw an unusual flare in this outfit. First, she adorned two beautiful halo twist that made her look queenly and ethereal but her outfit was out the opposite end of the spectrum in the best way possible.

She did some serious pattern play pairing a colorfully striped camo jacket over a bichrome romper. What brought it all together was the big gold hoop earrings she wore, as if they were created to be the mediator between earth goddess and trendsetter.

PHOTO: COURTESY HBO

So, kudos to Issa and the amazing style team in charge of the Insecure cast. They were able to give Issa a distinct visual voice throughout the seasons but still manage to help her elevate in ways the matched her personal growth in the show. Over the last three seasons Issa evolved from awkward black girl to style Queen.

PHOTO: COURTESY HBO

It is almost painful to have to wait a whole year for the next season but we have plenty of Insecure Recaps for you here to keep satisfied until then.

Comment below with your favorite Issa looks from any of the last three seasons!